As far as the gate checking strollers business goes (LOVED the unscientific comparison!) - it was the skycap in HNL that initially told us that we could not gate check the stroller. Since there were enough of us to keep her busy in the meantime, one member of our party hopped into the ticket area and asked one of the ticket agents who confirmed that they would not gate check a stroller. In Maui, it was the ticket agent at the check in desk who also told us to have the stroller checked in with TSA there, as it could not be gate checked. (We've flown on Aloha as well, and have gate checked the stroller with them with no problems.)
My (adult) brother and I were the only ones that flew back on go! (the rest of the family flew to the mainland direct from OGG), and the only carryons we had were one backpack each, and three bags of Krispy Kremes. So it's not like we were loaded down with stuff, but it was still a major PIA to have to carry my child through the airport to get to the gate.
I'd be happy to send in a letter to go!'s customer service department. I do have the name of the F/A on the second flight - they may just have to look up the name of the woman from the flight out.
Live and learn!
(kaukau - I apologize for my cluelessness - what airline is WP?)